menu010.png

Stereocontrolled formation of substituted imidazolidines in the reaction between N-metallated azomethine ylides and isocyanate.

Stereocontrolled formation of substituted imidazolidines in the reaction between N-metallated azomethine ylides and isocyanate. ARKIVOC. 2005, Vol. (ix), pp 189-199.

http://quod.lib.umich.edu/a/ark/5550190.0006.919/1/--stereocontrolled-formation-of-substituted-imidazolidines?page=root;size=150;view=text

Abstract:Substituted imidazolidines (and not imidazolidin-4-ones) are the unexpected cycloadducts obtained in the reaction between imines and isocyanates. The reaction is shown to take place via stepwise [3+2] cycloaddition between the N-metallated azomethine ylide formed in situ and the starting imine, followed by nucleophilic addition of the resulting imidazolidine on the sphybridized carbon atom of the isocyanate. Density-Functional Theory calculations provide a model for the mechanism of this unusual reaction and for the origins of the observed regio- and stereoselectivity.

 

   QUIMATRYX

   Paseo Mikeletegi 69, 3┬¬ planta

   20009 San Sebasti├ín

   Tel: 946 08 70 37

   www.quimatryx.com